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Screw epoxidation indole heterocyclic compound as well as synthetic method and purpose thereof

A technology of heterocyclic compounds and indoles, which is applied in the field of spirocyclic indole heterocyclic compounds, can solve problems such as the unstable structure of chrysanthemum-like antifeedants, and achieve improved antifeedant activity, stable structure, and mild reaction conditions Effect

Inactive Publication Date: 2014-06-11
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] The purpose of the present invention is to overcome the shortcomings of the unstable structure of the existing chrysanthemum-based antifeedants, and provide a spiro-ring oxindole heterocyclic compound containing enol thioether with relatively stable structure and low production cost.

Method used

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  • Screw epoxidation indole heterocyclic compound as well as synthetic method and purpose thereof
  • Screw epoxidation indole heterocyclic compound as well as synthetic method and purpose thereof
  • Screw epoxidation indole heterocyclic compound as well as synthetic method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] (1). Add 100mmol of benzyl bromide, 120mmol of thiophene boronic acid, 1.2mmol of Pd(PPh 3 ) 4 , 200mL ethylene glycol dimethyl ether and 100mL water, 200mmol of Na 2 CO 3 , heated to reflux at 100°C under the protection of nitrogen, reacted for 5 hours, removed the solvent under reduced pressure, and isolated to obtain Yield 90%.

[0061] (2). Add 80mmol of DMF and 100mL of dichloromethane into a 500mL single-necked flask, stir for half an hour, then slowly add 80mmol of POCl dropwise under ice bath conditions 3 , stirred at room temperature (25°C) for half an hour, then slowly added 20 mmol dropwise in ice bath Then placed at room temperature (25°C) and stirred for half an hour, heated to reflux at 50°C for 12 hours, added a strong base to alkalinize the system until the pH of the system was 7, and separated the liquid product to obtain, Yield about 95%.

[0062] (3). Add 5g to a 500mL single-necked flask 10g KMnO 4 , a mixed solution of 200 mL of acetone ...

Embodiment 2

[0072] The difference between this embodiment and embodiment 1 is: the reactant of step (5) for The compound obtained is: Its physical constants are:

[0073] 1 H NMR (400MHz, CDCl 3 )δ=7.46-7.44(m, 2H), 7.33-7.26(m, 2H), 7.20-7.17(m, 1H), 6.87(s, 1H), 6.73(s, 1H), 6.69(d, J= 6.0Hz, 1H), 6.48(s, 1H), 5.80(d, J=6.0Hz, 1H), 3.93(s, 3H), 3.82(s, 3H), 3.78(q, J=7.2Hz, 2H) , 1.31(t, J=7.2Hz, 3H);

[0074] 13 C NMR (100MHz, CDCl 3 )δ174.6, 150.8, 145.8, 142.8, 137.3, 136.7, 135.8, 132.4, 128.5, 128.2, 126.8, 121.0, 119.5, 109.8, 94.5, 56.8, 56.6, 35.6, 30.1, 12.9.

[0075] MS(ESI): m / z=280(M+H) + .

[0076] Elemental Analysis: C 22 h 21 NO 3 Calculated for S: C, 69.63; H, 5.58; N, 3.69; O, 12.65; S, 8.45 Found: C, 69.52; H, 5.71; N, 3.80; S, 8.59.

Embodiment 3

[0078] The difference between this embodiment and embodiment 1 is that the reactant of step (5) for The compound obtained is: Its physical constants are:

[0079]1 H NMR (400MHz, Acetone) δ=7.47-7.45(m, 2H), 7.38-7.34(m, 2H), 7.21-7.17(m, 1H), 6.73(s, 1H), 6.73(d, J=6.0 Hz, 1H), 6.37(s, 1H), 6.29(s, 1H), 5.88(d, J=6.0Hz, 1H), 3.86(s, 3H), 3.76(q, J=7.2Hz, 2H), 3.75(s, 3H), 1.22(t, J=7.2Hz, 3H);

[0080] 13 C NMR (100MHz, Acetone) δ174.76, 164.20, 158.86, 145.52, 145.35, 138.32, 137.76, 133.62, 129.33, 128.75, 127.17, 119.64, 105.97, 93.56, 89.86, 604.13, 56.1

[0081] MS(ESI): m / z=380(M+H) + .

[0082] Elemental Analysis: C 22 h 21 NO 3 Calculated for S: C, 69.63; H, 5.58; N, 3.69; O, 12.65; S, 8.45 Found: C, 69.82; H, 5.69; N, 3.77; S, 8.21.

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Abstract

The invention discloses a screw epoxidation indole heterocyclic compound is figured in the following structural formula. In the structural formula, Ar is C2-18 unsaturated alkyl, and R1 is H, C1-14 alkyl or C2-14 unsaturated alkyl; and R2 is H, C1-14 unsaturated alkyl, alkane, R3O or R4R5N; and R3, R4 and R5 are H, C1-14 unsaturated alkyl or alkane. The spiro oxidized indole heterocyclic compound is stable in structure and can be used as an insect antifeedant. The screw epoxidation indole heterocyclic compound has the benefits that the screw epoxidation indole heterocyclic compound is specially synthesized into furfuryl alcohol compound through taking lewis acid as a catalyst, the use of a lithium reagent is avoided, and the cost is reduced; and meanwhile, a synthetic method has the characteristics of mild reaction conditions, simplicity and convenience, and specificity and can be used for industrial production.

Description

technical field [0001] The present invention relates to a spiro-ring oxindole heterocyclic compound, namely, a spiro-ring oxindole heterocyclic compound with a saturated side chain and an enol thioether structure and a method for synthesizing the compound with a Lewis acid as a catalyst , and the compound has insect repellant activity, and can be used as an insect repellant. Background technique [0002] The current protective measures for crops mainly rely on the application of broad-spectrum chemical insecticides. Although these compounds are very practical and effective, their shortcomings are also obvious; first, because these compounds are rarely selective in killing insects, they often kill At the same time as the pests, the natural enemies of the pests are also doomed. After the pests develop resistance, they need to increase the dose of insecticides to achieve the purpose of killing the pests. The consequence of such a vicious circle is the destruction of the ecologi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/10A01N43/90A01P15/00
Inventor 尹标林黄力
Owner SOUTH CHINA UNIV OF TECH
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